Zinc pyrithione

Zinc pyrithione

Names
IUPAC name bis(2-pyridylthio)zinc 1,1'-dioxide
Other names ZnP, pyrithione zinc, zinc OMADINE
Identifiers
CAS Number	13463-41-7 Y
3D model (JSmol)	Interactive image
ChemSpider	21513957 Y
ECHA InfoCard	100.033.324
PubChem CID	3005837
UNII	R953O2RHZ5 Y
InChI InChI=1/C5H5NOS.Zn/c7-6-4-2-1-3-5(6)8;/h1-4,7H;/q;+2 Key: YUYSACQNSLQTMI-UHFFFAOYAS
SMILES c1cc[n+]2c(c1)S[Zn-2]3(O2)O[n+]4ccccc4S3
Properties
Chemical formula	C10H8N2O2S2Zn
Molar mass	317.70 g/mol
Appearance	colourless solid
Melting point	240 °C (464 °F; 513 K) (decomposition)
Boiling point	decomposes
Solubility in water	8 ppm (pH 7)
Pharmacology
ATC code	D11AX12 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Zinc pyrithione (or pyrithione zinc) is a coordination complex of zinc. It has fungistatic (that is, it inhibits the division of fungal cells) and bacteriostatic (inhibits bacterial cell division) properties and is used in the treatment of seborrhoeic dermatitis.

The pyrithione ligands, which are formally monoanions, are chelated to Zn²⁺ via oxygen and sulfur centers. In the crystalline state, zinc pyrithione exists as a centrosymmetric dimer (see figure), where each zinc is bonded to two sulfur and three oxygen centers. In solution, however, the dimers dissociate via scission of one Zn-O bond.

This compound was first described in the 1930s.

Pyrithione is the conjugate base derived from 2-mercaptopyridine-N-oxide (CAS# 1121-31-9), a derivative of pyridine-N-oxide.

Zinc pyrithione is best known for its use in treating dandruff and seborrhoeic dermatitis, particularly in dandruff shampoos. It also has antibacterial properties and is effective against many pathogens from the and Staphylococcus genera. Its other medical applications include treatments of psoriasis, eczema, ringworm, fungus, athletes foot, dry skin, atopic dermatitis, tinea, and vitiligo.